(S)-4,5-dihydroxypentane-2,3-dione

Base Information

• Chemical Name: (S)-4,5-dihydroxypentane-2,3-dione
• CAS No.: 710324-30-4
• Molecular Formula: C5H8 O4
• Molecular Weight: 132.116
• European Community (EC) Number: 636-098-2
• Nikkaji Number: J1.969.645F
• Wikipedia: 4,5-Dihydroxy-2,3-pentanedione
• Wikidata: Q27110096
• Metabolomics Workbench ID: 54078
• ChEMBL ID: CHEMBL193493
• Mol file: 710324-30-4.mol

Synonyms:1-deoxypentosone;4,5-DHP;4,5-dihydroxy-2,3-pentanedione

Chemical Property of (S)-4,5-dihydroxypentane-2,3-dione

Chemical Property:

• Boiling Point: 263.0±30.0 °C(Predicted)
• PKA: 11.36±0.20(Predicted)
• PSA: 74.60000
• Density: 1.311±0.06 g/cm3(Predicted)
• LogP: -1.50230
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 129

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(=O)C(CO)O
• Isomeric SMILES: CC(=O)C(=O)[C@H](CO)O

Technology Process of (S)-4,5-dihydroxypentane-2,3-dione

There total 13 articles about (S)-4,5-dihydroxypentane-2,3-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

(S)-4,5-cyclohexylidenedioxy-2,3-pentanedione (848035-01-8) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4,188674-57-9)

Guidance literature:

(S)-4,5-cyclohexylidenedioxy-2,3-pentanedione; With sulfuric acid-d2; In dimethylsulfoxide-d6; water-d2; for 6h;

aq. phosphate buffer;

DOI:10.1021/ja802353j

Reference yield:

S-ribosyl-L-homocysteine (β-form) → L-homocysteine (6027-13-0) + (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4,188674-57-9)

Guidance literature:

With MES buffer; E_. coli S-ribosylhomocysteinase; S-<(3-carboxy-4-nitrophenyl)thio>-2-aminoethanethiol; pH=6; Further Variations:; Reagents; pH-values; Enzyme kinetics; Kinetics; Enzymatic reaction;

DOI:10.1021/ol048404+

Reference yield:

(R)-pent-3-yne-1,2-diol (500596-40-7) → (4S)-4,5-dihydroxy-2,3-pentanedione (710324-30-4,188674-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 814 mg / sulfuric acid / 1 h / 20 °C

2: 10 percent / potassium permanganate; MgSO₄; NaHCO₃ / acetone; H₂O / 0.33 h / 20 °C

3: H₂O; aq. phosphate buffer; NaCl / 36 h / pH 6.5

With potassium permanganate; phosphate buffer; sulfuric acid; water; sodium hydrogencarbonate; magnesium sulfate; sodium chloride; In water; acetone;

DOI:10.1002/anie.200353150

upstream raw materials:

1-(2-methoxy-[1,3]-dioxolan-4-yl)-propane-1,2-dione

2-methoxy-4-(prop-1-ynyl)-[1,3]-dioxolane

(R)-pent-3-yne-1,2-diol

(R)-2,2-Dimethyl-4-prop-1-ynyl-[1,3]dioxolane

Refernces

• 1、 Marques, Joao C.,Lamosa, Pedro,Russell, Caitlin,Ventura, Rita,Maycock, Christopher,Semmelhack, Martin F.,Miller, Stephen T.,Xavier, Karina B.. "Processing the interspecies quorum-sensing signal autoinducer-2 (AI-2): Characterization of phospho-(S)-4,5-dihydroxy-2,3-pentanedione isomerization by LsrG protein". experimental part. p. 18331 - 18343. Retrieved 2012/04/10.
• 2、 Ganin, Hadas,Tang, Xu,Meijler, Michael M.. "Inhibition of Pseudomonas aeruginosa quorum sensing by AI-2 analogs". supporting information; experimental part. p. 3941 - 3944. Retrieved 2010/03/25.